The purpose of this article is to present an application of fuzzy logic to human reasoning about electronic commerce (e-commerce) transactions. This article uncovers some of the hidden relationships between critical factors such as security, familiarity, design, and competitiveness. We analyze the effect of these factors on human decision process and how they affect the Business-to-Consumer (B2C) outcome when they are used collectively. This research provides a toolset for B2C vendors to access and evaluate a user’s transaction decision process and also an assisted reasoning tool for the online user. © 2006, IGI Global. All rights reserved.